Phosphorus oxychloride → 3,6-Dichloropyrido[2,3-b]pyrazine

HRID 2199906ノート

反応式

HRID 2199906 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][C:8](=O)[NH:9][C:10]=2[N:11]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:8]1[N:9]=[C:10]2[N:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:6][CH:7]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 866975626-Chloropyrido[2,3-b]pyrazin-3(4H)-one

生成物 1

HCID 866975633,6-Dichloropyrido[2,3-b]pyrazine収率 90%

実験手順

6-chloropyrido[3,2-b]pyrazin-3(4H)-one (E-27) (9 g, 49.8 mmol) was dissolved in POCl3 (100 mL) and the resulting mixture was stirred at reflux for 3 h. The reaction was complete based on TLC analysis. The mixture was cooled to RT and concentrated in vacuo to remove POCl3. The residue was poured into ice water (150 mL) and extracted with DCM (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the desired product 3,6-dichloropyrido[2,3-b]pyrazine (E-28) (9 g, 90% yield) as a solid. ESI-MS m/z: 199.97 [M+H]+.

後処理

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. customto remove POCl3
  4. additionThe residue was poured into ice water (150 mL)
  5. extractionextracted with DCM (3×100 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-9599de175ee44bc5aa58c152b05d7b02
出典データセット
uspto-grants-2016_06
特許番号
US09359352B2

反応ノート

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